Aryl pseudohypochlorites - some reactions with Lewis acids

Several aryl hypochlorites were prepared by the action of chlorine on the sodium salts of substituted phenols. Infrared and ultraviolet spectral data confirmed a rearrangement of the resulting hypochlorites into ortho and para quinoid forms Frledel-Crafts reactions were carried out with the pseudohypochlorites with either benzene or benzene or anisole. Aluminum chloride was used as the catalyst. Analysts of these reactions showed two concurrent but distinctly different reactions taking place. In one case, the pseudohypochlorites acted as a source of chloronium ions, causing chlorination of the solvent and regenerating the original substituted phenol. In the other reaction, it appeared that an an intermediate oxyphenonium ion may have been generated, which on reaction with the solvent produced a diphenyl ether derivative. The Frledel-Crafts reaction of the pseudohypochlorlte of tetrabromobisphenol-A and benzene yielded a complex mixture of chlorine and bromine trisubstituted phenols